The rich guy who believes in having fun with his cash, buying rich parties, helicopters, trips to the Titanic, whatever. This guy is definitely more fun than the standard tightwad image that accompanies most millionaires.

He also might just be an excuse for the main characters to be able to spend their time doing something besides earning money, since this guy is keeping them fed. When the writers of a comedy aren't in the mood to come up with a unique premise, he may also have set up a bet/challenge/goofy will/whatever for a huge amount of cash; hilarity ensues of course.

Examples

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Anime and Manga

Honey, Sunako's aunt in The Wallflower who spends her time globe-trotting in a helicopter and schmoozing at parties. She also wants her dark niece to turn into a lady, and gives the job to four Bishōnen in exchange for free rent in a mansion...if they succeed.

Lory Takarada, from Skip Beat!, seems to believe that you couldn't enter in any building without a parade imported from the Rio de Janeiro's Carnival and dressing like the lovechild of Charirman Kaga and Walter Mercado. And pray he doesn't hear that you're planning a party, because he'll bring you the same design team who decorated Willy Wonka's factory. Well, he is the president of a big talent agency, so his eccentricities can be sightly handwaved, but still...

To a certain degree, Gary Oak from Pokémon. He is fairly rich, due to Professor Oak's research, and would easily qualify seeing as he not only spends all of his money buying cruise tickets, a week at the spa, a sports car most people would dream about and his faithful busty cheerleaders. He's ten, for Christ's sake.

Not to mention, spending your fortune on travelling across the world searching for pets (in a nutshell) is... Pretty wacko in itself.

Ouran High School Host Club...the Club itself, but hell, the entire freaking Ouran Academy. When Haruhi says "Rich Bastards" she isn't kidding!

Love Live! Sunshine!! features Mari Ohara, the teenage heiress to a world-class hotel chain. Drama CDs show that she can and will, if not stopped, bring home stray sea creatures as pets and treat them to high-quality, expensive diets, and aside from that, the anime shows that she has so much time and money on her hands that she (a high school student) created her own stew out of expensive ingredients she procured around the world. Also she bought the director's position at her own school, which she still studies at as a third-year student.

Comic Books

Bruce Wayne, who, as a Rich Idiot with No Day Job, has a public image as above, but his real eccentricity is that he is the superhero, Batman (and borderline psychopath, depending on the writer).

Surprisingly, Marvel's Hercules. After his death, Namora and Venus go about trying to put all his affairs in order, and discover he owns everything from pleasure resorts to a hospital/orphanage for the children of mythological monsters. Also, a good chunk of his still-living ladies were gifted homes. Apparently, he made a few really smart investments, then just never bothered to keep up with them and bought whatever he damn pleased on the (correct) assumption that he just could.

The deceased uncle in the various film (and theatrical) adaptations of Brewster's Millions (named Rupert in the Richard Pryor version, but given different names in other versions). Part of the bit is that he was the classic skinflint tycoon in life, but had enough guile to leave a booby trap in his will intended to make his inheritor hate spending money.

The Magic Christian revolves around Sir Guy Grand, a millionaire who uses his fortune to play cruel practical jokes on others.

Peter Sellers, who played Grand in the film (it was adapted from an earlier novel), was an excellent real-life example of this. In particular his passion for cars was so infamous it was referenced in The Goon Show and a sight gag in the short film Simon, Simon (his lovely sports car is run into; he steps out, snaps his fingers, and a new one in a different color is wheeled out for him to drive off in). His poor money management due to his tastes left him almost insolvent in the early 1970s. He was also a practical joker, but less cruel and destructive than Grand.

Felix Happer of Local Hero, a Big Oil executive whose office doubles as a planetarium and is willing at the end to spend untold millions setting up a center for marine and astronomy research instead of building an oil refinery.

Adam Sandler's uncle in Mr. Deeds fits the description before he dies.

Tony Stark as portrayed by Robert Downey, Jr. in the Iron Man movies. He buys million-dollar paintings just because they're overpriced, but dislikes being handed anything. He flies to Monaco to watch an F1 race, but decides at the last minute to instead actually compete. Getting the picture?

Literature

Joe Bob Fenestre from Animorphs presents this image to the public. The truth is altogether more sinister.

Samuel Westing of The Westing Game fits this trope. He loved fire works, playing dress up, and generally messing with people. He also involves all the main characters (one of which turned out to be him) in a complicated game for his inheritance.

Elon Tessic of Shattered Sky is an eccentric multibillionaire who wants to spend his fortune in unusual ways. In one of his earliest scenes, we see him buy a restaurant-owner friend's pie recipe for millions of dollars.

Mr Toad in The Wind in the Willows could be a deconstruction on this trope; he enjoys blowing his inherited money on whatever he thinks is most enjoyable, from a caravan, to a motor car, but got in trouble when his obessive with motor cars went too far. And he risks losing his fortune on his obsessives when he could have used it responsibly to help him live his entire life comfortably.

Hubertus Bigend, the massively wealthy and Bunny-Ears Lawyer-ish advertising exec whose plans and interests form the core of William Gibson's Bigend Books.

Never quite confirmed if he is a millionaire, as his income is only described as "six craploads a year", but Barney Stinson from How I Met Your Mother qualifies if so. He has spent money on two TV's that cover an entire wall, as well as many different contraptions to upgrade his apartment and as props in his ridiculously convoluted schemes to seduce women. During a fit of rage, he once smashed a TV that was discarded in a dumpster and the Running Gag of the episode has him smashing a TV from the dumpster every time he gets upset. When the dumpster ran out of TVs, he freaked out, went to a nearby store and bought a brand new flatscreen HD TV so he could smash it.

John Beresford Tipton, the mysterious Millionaire from the series of the same name. Even though he doesn't actually appear on screen, he acts as a trickster by throwing a disruptive catalyst (i.e., a check for a million dollars) into people's lives.

Chairman Kaga in Iron Chef and his nephew Chairman Mark in Iron Chef America. The former is on record as stating he spent ¥843,354,407 just on ingredients for Kitchen Stadium (roughly $8 million at the time), while the latter has several Kitchen Stadiums built (including one In Space). And let's remember, this is to host Cooking Duels. If that ain't eccentric...

Thurston Howell III on Gilligan's Island. He's so eccentric he uses his money as leverage on a deserted island.

In the 2007-09 series Life, Detective Charlie Crews definitely fits the bill. (If you were in the LAPD and they railroaded you for a murder you didn't commit, then you were exonerated years later and received a multi-million dollar settlement from the LAPD for your false imprisonment, would you really go back to work for the LAPD?)

In one episode, Crews encounters a support group for multi-multi-million dollar lottery winners. At the end of the episode, Crews asks if he can join the group. He tells them that he didn't win the lottery, per se. However, his settlement amount (which he is forbidden to disclose) would otherwise qualify him for membership in their club.

One of the lottery winners in that episode had become so paranoid that he became a gun hoarder who built a high cinder block wall around his house.

John Hodgman has a reoccurring part as a "Deranged Millionaire" on The Daily Show.

What Could Have Been — Ted Allen, host of the popular cooking/food show, Chopped, humorously remarked that the show was originally going to take place in an eccentric millionaire's mansion, with the millionaire's butler as the host and the losing dishes being fed to the millionaire's pet Chihuahua. Naturally, the Food Network found this "too weird," but wanted to keep the general premise of the show and put it in a more straightforward competition format.

Music

The Deranged Millionaire, a recurring character from the work of They Might Be Giants, played by author and comedian John Hodgman. He hosts the music video compilation/Concept Album "Venue Songs" (and figures into the Myth Arc explaining the project), and has appeared in some of their stage performances and podcasts. See Literature, above. The band wrote a themesong for him, called "Yeah, The Deranged Millionaire''.

He lived in a secret location, burnin' money all day And people from miles around were miles away''

Video Games

In Captain Morgane and the Golden Turtle, the rich merchant funding Morgane's expedition considers himself to be this (with "eccentric" being his preferred softer alternative to things like "mad" or "crazy", which is what people who know his objective tend to call him).

Western Animation

Señor Senior Senior and his son, Señor Senior Junior, on Kim Possible. After some unwitting suggestions from Ron, SSS decides to take up villainy as a hobby (and as a way to bond with his son), strictly adhering to Cartoonish Supervillainy for the fun of it, and SSJ's obsessed with his appearance and becoming a world famous celebrity (usually a pop singer of some kind).

Super Chicken from George of the Jungle. His identity is millionaire playboy Henry Cabot Henhouse III (Hunt Strongbird Jr. in the unaired pilot).

An episode of American Dad! has a popular hair dresser, named Beauregard, who moves to New York City from Langley Falls to carry on the city's tradition of "wealthy obnoxious weirdos".

Sir Iknik Blackstone Varrick in The Legend of Korra is a profound case of this. Unfortunately, people forget that there has to be competence beneath the eccentricity for him to have created his fortune, and he is able to serve as a recurring villain before anybody even considers suspecting him.

Real Life

Canadian financier Charles Vance Millar was an infamous practical joker. His best-known eccentricity was the Great Stork Derby, wherein Millar, having no heirs at the time of his death, left the majority of his estate to the Canadian woman who gave birth to the most children in the ten years following his death. Truth in Television, indeed.

The late Steve Fossett. He flew around the world in a balloon and a jet that didn't need refueling, both times solo, and set more world records than can be recorded here.

Billionaire clown (and CEO of Cirque du Soleil) Guy Laliberté plays high-stakes poker for fun and does quite well, possibly because the money involved is nowhere near enough to make a difference to him. In 2012, he announced a $1 million buy-in tournament to raise money for a charity he founded. He's also been into space.

Philadelphia socialite Anthony J. Drexel Biddle (1874-1948) is an early real-life example of this trope. His wealth allowed him to pursue interests such as the theater, politics, self-published literature, religious study and physical fitness (particularly boxing) at his leisure. He also kept alligators as pets in his home. A novel, play and film were based on him and his eccentricities.

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